HCID 68295045, compound → HCID 68295303, compound

HRID 1909323Notes

Reaction equation

HRID 1909323 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:17]([NH:19][CH2:20][C:21]2[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])=[O:18])[C:6]2[CH:7]=[N:8][N:9]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:10]=2[CH:11]=1>CO.[Pd]>[CH:12]1([N:9]2[C:10]3[CH:11]=[C:3]([CH3:2])[CH:4]=[C:5]([C:17]([NH:19][CH2:20][C:21]4[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=4[CH3:27])=[O:18])[C:6]=3[CH:7]=[N:8]2)[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 68295045HCID 68295045, compound

Product 1

HCID 68295303HCID 68295303, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-(bromomethyl)-1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydro pyridine-3-yl)methyl)-1H-indazole-4-carboxamide (0.05 g, 0.13 mmol) was dissolved in methanol (2 mL) and Pd—C (10%, 0.01 g) was added to it. The resulting reaction mixture was stirred at room temperature for 1 h. On completion, the reaction mixture was filtered and concentrated to obtain solid compound which was washed with ether and pentane affording pure target compound (0.045 g, 91.89%). LCMS: 379.30 (M+1)+; HPLC: 98.15% (@ 254 nm) (Rt;6.603); 1H NMR (CD3OD, 400 MHz) δ 8.28 (s, 1H), 7.63 (s, 1H), 7.48 (s, 1H), 6.70 (s, 1H), 5.12 (m, 1H), 4.61 (s, 2H), 2.56 (s, 3H), 2.55 (s, 3H), 2.42 (s, 3H), 2.19-2.14 (m, 2H), 2.12-2.04 (m, 2H), 2.00-1.92 (m, 2H), 1.82-1.75 (m, 2H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationOn completion, the reaction mixture was filtered
  3. concentrationconcentrated
  4. customto obtain solid compound which
  5. washwas washed with ether and pentane affording pure target compound (0.045 g, 91.89%)

Sources & evidence

ORD record
ord-a82907d7316b4389a7335f16dde73b56
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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